


Fortune Favors the Lovesick

by Winniwyn



Category: Critical Role (Web Series)
Genre: Alternate Universe - High School, Alternate Universe - Modern Setting, F/M
Language: English
Status: In-Progress
Published: 2019-12-20
Updated: 2019-12-20
Packaged: 2021-02-26 00:08:49
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,605
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21874189
Author URL: https://archiveofourown.org/users/Winniwyn/pseuds/Winniwyn
Summary: Part 1 of my Secret Santa gift in the Widojest server.Jester has some interesting ideas on how to get a boyfriend and finds a cat instead.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 2
Kudos: 31





	Fortune Favors the Lovesick

**Author's Note:**

  * For [pinkevilbob](https://archiveofourown.org/users/pinkevilbob/gifts).



Jester was down to her last quarter. She could almost hear the faint rumble of her stomach growling in protest at the prospect of going another day without lunch, but she was desperate. She’d stopped by this old rundown arcade before school every other day for the last two weeks. Every time she’d spend all of her lunch money on hoky old fortune-telling games in search of an answer to her heart’s deepest desire. She had to know: would she ever find true love? 

Most of the fortunes were about things she didn’t care about, like money or status, occasionally they even talked about health. Not that it wasn’t nice to be told you’d live a long fruitful life, but Jester was nearing the end of her high school years and hadn’t even been on a single date. By this point, all of her friends had experienced some sort of grand romantic adventure. Some had even been through the bitterness of heartache! Even her friend, Nott--who barely left her house-- had found a gentleman suitor in some distant sleepy town. There was no help for it; Jester was bound and determined to find a paramour of her own! 

Her tail swished nervously back and forth and felt the wind rustle in her hair. She stared down the line of ancient games that lined the outside of the arcade. Her eyes stopped on the word fortune and stared it down, feeling like she was about to enter into a shootout in an old western movie. She took a deep breath before pushing her quarter into the machine. Her eyes shut tight and Jester concentrated really, really hard on her amorous desires, trying to psychically will the machine to give her what she wanted. The machine whirred to life and lit up, the rickety old puppet inside running her chipped and discolored hand over the crystal ball that flashed with cheap lightning effects. The woman’s voice was faded and so robotic that Jester could barely make out the words, “My crystal knows what you seek, take this fortune and all will be revealed!”

Part of a small piece of paper shot out of a slot in the machine labeled ‘fortunes’. Jester snatched it greedily and held it against her chest for a moment, certain that this would be the one she’d been searching for. After a few quick breaths to calm herself Jester looked at the paper and read her fortune: Don’t worry about money, the best things in life are free!

Jester stared at the piece of paper for a few moments, completely stunned. Again? That couldn’t be right. How could she have invested so much time and like, probably 50 quarters or something on these machines and not get a single love fortune? She knew they were in there! Just a couple of months ago one of her classmates came in bragging about how the guy she liked asked her out the very next day after getting some romantic good luck from one of these things. 

“You stupid machine, I’m not worried about money I’m freaking rich already!” She yelled and tore the paper to shreds. “I just want to know what it’s like to fall in love, is that so much to ask?”

Jester kicked the machine with such force that it rocked back toward the wall it was resting against. There was a throbbing pain in her foot after making contact with the metal bolted into the corners but she ignored it, she was too busy thinking about how many dicks she was going to draw on the glass case that guarded the animatronic within. She almost didn’t notice the extra slip of paper that slipped out of the fortune slot as the machine settled back onto the ground. She blinked in surprise and read the words ‘your love-’ before a strong gust of wind swept up and blew the paper away. 

“Ah!” Jester tried to reach for the slip but the wind was strong enough that it just barely slipped her grasp. “Wait, come back!”  
She tried to run after it as fast as she could but it was all the way across the street by now and she had to stop for a passing truck. She huffed and jogged in place at the crosswalk, ready to dash across as soon as the coast was clear. She’d finally caught a lucky break and no gust of wind was going to take it from her. She’d chase it halfway across the city if she had to!

After crossing the street Jester could see the strip of paper just barely beginning to slip out of view on the crest of the small hill in front of her. Jester ran up the hill as fast as her legs would carry her, afraid of what might happen if she lost sight of the fortune. Another strong burst of wind blew past her and she knew that if she didn’t catch up to it now, it would be lost to her forever. She reached out, her fingertips barely brushing the edge of the paper. She almost had it! Just a little further and…

It was unfortunate that in her mad dash up the hill Jester had neglected to pay attention to the condition of the sidewalk. She felt her foot hit a piece of jagged cement and flailed her arms wildly. Her heart sank into the pit of her stomach, lurching downward with the rest of her body. Jester landed with a thud, face first down onto the pavement and her fortune slipped out of her grasp.

That was it, all that determination, energy, and lunch money wasted. Jester felt that brief spark of hope drain from her; she may as well abandon her chase. But out of the corner of her eye she watched a dark, furry shape leap out of the bushes and snatch the little slip of paper just as it was about to disappear over the crest of the hill. Jester groaned and looked up towards the creature and its yellow eyes gleamed down at her, the fortune clutched in its jaws. 

“Aww, what a cute little kitty cat!” Jester sat up, wincing a little from a scrape on her knee. “You have no idea how much trouble you just saved me kitty, it must really be my lucky day!”

The small spotted cat tilted its head to the side.

“Now if you could just give me that paper please…Mr. Kitty” Jester slowly reached for the fortune in the cat’s mouth but stopped abruptly when she heard a low, throaty growl. “Pretty please?”

Jester dared to inch her hand a little closer to the cat’s mouth and it’s brown spotted fur began to bristle. The cat stared into her eyes with an intensity she was not expecting from a common house pet and the moment she faltered and started to draw back, the cat began to eat her love fortune. Jester shrieked and grabbed the animal. She briefly thought about shaking the cat until it threw up, but managed to curb the impulse, not wanting to actually harm the animal. Especially not for something as trivial as a love fortune from a cheap arcade game that probably wouldn’t come true anyway.

She let out a melodramatic sob and shook her head, “Guess it’s not my lucky day after all.”

The cat only meowed. 

Jester looked at the cat and only then did she notice the tag that hung from the collar on its neck. The cat must belong to someone, so what was it doing out here, all alone on the sidewalk? She took a moment to examine the cat further and noticed it also had a harness. Jester gasped when she noticed the leash tangled in the bushes next to them. 

“Where is your owner Mr. Kitty? Or um…” Jester lifted the cat up higher and angled her head. “Yes, definitely Mr. kitty. I think. To be honest I’ve never really had a cat before so I’m not one hundred percent sure but I’m pretty sure those are b-”

The cat put a gentle paw to Jester’s lips.

“You’re right, this is no time to talk about genitals!” she said, putting him back on the ground. She looked at the cat and it looked up at her. She crouched down next to him and cradled her chin in the palm of her hand. “If you have an owner then you must have a name…”

She reached for the tag on the cat’s caller and squinted at the writing. It said something but it was in one of those hard to read fancy-dancy fonts that the average person would never be able to read properly. Fortunately, Jester came from money and prestige...but even she was having a hard time reading it. 

“R-Rumpl...No.” She stuttered and tilted the tag in another direction.” Fr...Hmm...Oh! Pumpkin! Your name is Pumpkin!” 

Pumpkin meowed.

“Weird name for a cat that’s not even orange but different strokes for different folks I guess!” Jester frowned at Pumpkin. “Well Pumpkin, what should I do with you?”

Meow.

“You’re right, we need to find your owner.” She said. “But it’s not like I can take you to school with m--Oh my gosh! School!”

Meow?

“Oh my gosh, oh no! Mrs. Vysoren is going to kill me if I’m late again!”

And with that Jester untangled Pumpkin’s leash from the nearby bushes while he purred and rubbed against her legs, scooped the little spotted cat up in her arms, and dashed haphazardly back down the hill.


End file.
